Dipolar Dyes with a Pyrrolo[2,3‐<i>b</i>]quinoxaline Skeleton Containing a Cyano Group and a Bridged Tertiary Amino Group: Synthesis, Solvatofluorochromism, and Bioimaging

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  • Łukasz G. Łukasiewicz
    Institute of Organic Chemistry Polish Academy of Sciences Kasprzaka 44/52 01-224 Warsaw Poland
  • Irena Deperasińska
    Institute of Physics Polish Academy of Sciences Al. Lotników 32/46 02-668 Warsaw Poland
  • Yevgen M. Poronik
    Institute of Organic Chemistry Polish Academy of Sciences Kasprzaka 44/52 01-224 Warsaw Poland
  • Yong Woong Jun
    Department of Chemistry POSTECH 77 Cheongam-Ro, Nam-Gu Pohang, Gyungbuk 37673 Korea
  • Marzena Banasiewicz
    Institute of Physics Polish Academy of Sciences Al. Lotników 32/46 02-668 Warsaw Poland
  • Bolesław Kozankiewicz
    Institute of Physics Polish Academy of Sciences Al. Lotników 32/46 02-668 Warsaw Poland
  • Kyo Han Ahn
    Department of Chemistry POSTECH 77 Cheongam-Ro, Nam-Gu Pohang, Gyungbuk 37673 Korea
  • Daniel T. Gryko
    Institute of Organic Chemistry Polish Academy of Sciences Kasprzaka 44/52 01-224 Warsaw Poland

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<jats:title>Abstract</jats:title><jats:p>Two strongly polarized dipolar chromophores possessing a cyclic tertiary amino group at one terminus of the molecule and a CN group at the opposite terminus were designed and synthesized. Their rigid skeleton contains the rarely studied pyrrolo[2,3‐<jats:italic>b</jats:italic>]quinoxaline ring system. The photophysical properties of these regioisomeric dyes were different owing to differing π conjugation between the CN group and the electron‐donor moiety. These dipolar molecules showed very intense emission, strong solvatofluorochromism, and sufficient two‐photon brightness for bioimaging. One of these regioisomeric dyes, namely, 11‐carbonitrile‐2,3,4,5,6,7‐hexahydro‐1<jats:italic>H</jats:italic>‐3a,8,13,13b‐tetraazabenzo[<jats:italic>b</jats:italic>]cyclohepta[1,2,3‐<jats:italic>jk</jats:italic>]fluorene, was successfully utilized in two‐photon imaging of mouse organ tissues and showed distinct tissue morphology with high resolution.</jats:p>

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